Alkaminester.



various methods; but We prefer to UNITED STATES PATENT orrron FRIEDRICHSTOLZ AND BAPTIST REUTER, OF HOCHST-ON-THE-MAIN,

GERMANY, ASSIGNORS TO FARBWERKE, VORM. MEISTER, LUOIUS 86 BRUNING, OFHQOHST-ON-THE-MAIN, GERMANY, A CORPORA- TION OF GERMANY.

I ALKAmmEs-rim.

Specification of Letters Patent.

Patented May 15, 1906.

Application filed December 2, 1905. Eerial No. 289,957.

To 00% whom it may concern.-

Be it known that we, lFRrEDRIoH S'ro z, Ph. D;, and BAPTIST REUTER, Ph.1)., chemists, both subjects of the Em eror of Germany, residing atHochst-on-t e-Main, Ger many, have invented certain new and usefulImprovements in the Pre aration of Alkaminester's, of which the folowing is a specification. I

We have found new substances valuable for pharmaceutical purposes. Theyare the alkaminesters of alkylated aminobenzoic acids. Said compoundsare obtainable by repare them b esterifying alkylated amino enzoic acidswith alkamins.

The alkaminesters of alkylated aminobenzoic acids are colorlesscompounds, little soluble in water, readil soluble in alcohol, ether,and benzene, an of alkaline reaction on litmus. vThe form hydrochloridewhich are readily solub e in water with a neutral reaction. When heatedWith alkalies or acids,' these alkaminesters are decomposed into alklated aminobenzoic acids and alkamins. T ey have a local anestheticaction, for which purpose the neutral reacting hydrochlorids areespecially suited.

The alkaminesters of alk lated aminobenzoic acids may be prepare forinstance, as follows: twelve parts, b weight, of aramethylaminobenzoicaci are intro need while stirring and cooling with ice into fifty parts,by weight, of sulfuric acid of ninety-six per cent. strength, to whichare allowed to dro ten parts, by weight, of diethylaminethano Themixture is heated for'six hours on the water-bath and when cold ispoured on ice. While cooling, it is made alkaline with ammonia and theseparated oil is extracted with ether. The ethereal solution being driedwith potash, there remains, after evaporating the ether, an oil, fromwhich when heated to about 120 centigrade in a vacuum somediethylaminethanol may be eliminated. The alkaminester thus obtained ispurified by. transforming it into the neutral hydrochlorid readilysoluble in water and alcohol, but which or stallizes from alcohol onaddition of ether. t melts at 108-109 centigrade.

The ara-methylaminobenzoic acid ester of diet laminethanol separatedfrom said hydroch orid is an oil which solidifies with dlfiiculty in thecold. It is readil soluble in alcohol, ether, and benzent; so uble withdifliculty in water.

Other alkamins may also be combined with other alkylated aminobenzoicacids, and thus other alkaminesters may be obtained having the samecharacteristic properties as above stated.

Having now described our invention, What we claim is- 1. As newproducts, the'alkaminesters of alkylated amlnobenzoic acids which aredecomposed when heated with acids or alkalies into alkylatedaminobenzoic acidsand alkamins, being colorless compounds, littlesoluble in water, readily soluble in alcohol, ether and benzene, formingwith hydrochloric acid readily-soluble salts of neutral reaction andhaving an anesthetic action free from irritating properties.

2. As new product, the dieth laminoethanolester of para methylaminoenzoic acid, a colorless compound decomposed when heated with alkaliesor acids into paramethylaminobenzoic acid and diethylaminoethanol andmelting below 0 centigrade, little soluble in Water, readily soluble inalcohol, ether and benzene, of alkaline reaction on litmus, forming withone e uivalent of hydrochloric acid a salt the so ution of which is ofneutral reaction having an anesthetic effect free from irritatingroperties.

In testimony that we 0 aim the foregoing as our invention we have signedour names in presence of two subscribing Witnesses.

FRIEDRICH STOLZ. BAPTIST REUTER.

Witnesses JEAN GRUND, (JARL GRUND.

